Please use this identifier to cite or link to this item: http://localhost:8080/xmlui/handle/123456789/1480
Title: Titanium-catalyzed hydroalumination of conjugated dienes: Access to fulvene-derived allylaluminium reagents and their diastereoselective reactions with carbonyl compounds
Authors: Jomy Joseph
Jaroschik, F
Harakat, D
Radhakrishnan, K V
Vasse, J-L
Szymoniak, J
Keywords: Titanium-catalyzed hydroalumination
Conjugated dienes
Allylaluminium reagents
Diisobutylaluminium hydride (DIBAL-H)
Carbonyl compounds
Issue Date: 2014
Publisher: Wiley
Citation: Chemistry - A European Journal 20(18):5433-5438;25 Apr 2014
Abstract: The described titanium-catalyzed hydroalumination of conjugated dienes opens up a new way to allylaluminium reagents. The reaction is carried out by using diisobutylaluminium hydride (DIBAL-H) and a catalytic amount of[Cp2TiCl2 (Cp=cyclopentadienyl). When applied to monoand disubstitued pentafulvenes, this reaction proceeds in a highly endocyclic manner. The formed allylaluminium compounds react regio- and stereoselectively with both aldehydes and ketones to afford homoallylic alcohols that are suitable synthons for functionalized cyclopentanones. An extension of this methodology to simple dienes was also investigated. In the proposed mechanism, the initially formed bimetallic species (Ti/Al) are involved in the two possible catalytic cycles with a direct hydroalumination or/and a hydrotitanation followed by a titanium to aluminium transmetallation.
ISSN: 1521-3765
Appears in Collections:2014

Files in This Item:
File Description SizeFormat 
  Restricted Access
403.29 kBAdobe PDFView/Open Request a copy

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.